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I wouldnt say he researched it persay because how was he supposed to know held have to protect the SH from the marines. He needed to send them safe fast because Luffy did something noones ever done. If he was going to just send them away he would have done it when he first saw them

They were put in a dangerous position where they needed to become stronger, so in order to keep them alive he sent them places he knew would make them stronger. It was a spur of the moment thing and really he sent them after they really needed to improve and avoid the marines.

The only one I believe could have been planned was Robin but it would have been to hard just to send her away or give her a reason to stay with the RA. In the end it was all a matter of circumstance and Kuma needed react quick to protect them.

very interesting theory!
It was obvious that all the locations he sent the SH-members were anything except coincidence, only the destination luffy landed on doesn't make sense, except the marines would never look for luffy there, and Boa is a well-trained haki-user?
I think this was one of the last assignments from Dragon before his son embarges into the NW perhaps? And before being transformed into a mindless human weapon.
I don't really get it why he would do that either, but maybe it's also in dragons plan, so he can try to duplicate the pacifista-weapons and enlarge his rebbelion-forces. (with the help of another genious scientists or somthing like that)
Or maybe for some personal reasons still unknown to us.